On the mechanism of [Rh(CO)2Cl]2-catalyzed intermolecular (5 + 2) reactions between vinylcyclopropanes and alkynes

Journal of the American Chemical Society

Volumn 126, Issue 30, 2004, Pages 9154-9155

  Yu, Zhi Xiang ^a   Wender, Paul A ^b   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CYCLOPROPANE DERIVATIVE; RHODIUM DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; ENERGY; LIGAND BINDING; MOLECULAR INTERACTION; OXIDATION; REACTION ANALYSIS;

EID: 3342979429     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048739m     Document Type: Article

References (29)

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15. Subsequent studies by our and other groups have shown that some (5 + 2) reactions can also be effected with other catalysts: see refs 1d, 11. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075. Binger, P.; Wedmann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 113. Wang, B.; Cao, P.; Zhang, X. Tetrahedron Lett. 2000, 41, 8041. Wender, P. A.; Love, J. A.; Williams, T. J. Synlett. 2003, 1259. Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Schirok, H. Org. Lett 2003, 5, 4149 and references therein.
16. Subsequent studies by our and other groups have shown that some (5 + 2) reactions can also be effected with other catalysts: see refs 1d, 11. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075. Binger, P.; Wedmann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 113. Wang, B.; Cao, P.; Zhang, X. Tetrahedron Lett. 2000, 41, 8041. Wender, P. A.; Love, J. A.; Williams, T. J. Synlett. 2003, 1259. Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Schirok, H. Org. Lett 2003, 5, 4149 and references therein.
17. Subsequent studies by our and other groups have shown that some (5 + 2) reactions can also be effected with other catalysts: see refs 1d, 11. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075. Binger, P.; Wedmann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 113. Wang, B.; Cao, P.; Zhang, X. Tetrahedron Lett. 2000, 41, 8041. Wender, P. A.; Love, J. A.; Williams, T. J. Synlett. 2003, 1259. Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Schirok, H. Org. Lett 2003, 5, 4149 and references therein.
18. Subsequent studies by our and other groups have shown that some (5 + 2) reactions can also be effected with other catalysts: see refs 1d, 11. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075. Binger, P.; Wedmann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 113. Wang, B.; Cao, P.; Zhang, X. Tetrahedron Lett. 2000, 41, 8041. Wender, P. A.; Love, J. A.; Williams, T. J. Synlett. 2003, 1259. Trost, B. M.; Shen, H. C.; Schultz, T.; Koradin, C.; Schirok, H. Org. Lett 2003, 5, 4149 and references therein.
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22. 298K (values in parentheses shown in Figures 2 and 4) are the calculated relative free energy and enthalpy at 298 K, respectively. Citations of the computational methods and references are given in Supporting Information.
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24. For the relative energies of other conformers of the stationary points shown in Figure 2, see Figure S1 of the Supporting Information.
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